As for the preparation of 2-hydroxy-1-indanone, several processes such as hydrolysis of the corresponding acetate have been known. However, processes directed to the preparation of optically active substances are very few and only the following two processes have been reported. One of them is effected by treating an alkyl-substituted siloxyindene with an oxidizing agent in the presence of an optically active manganese complex catalyst followed by desilylation [Kokai Tokkyo Koho Hei 7-228586 (1995)]. This process, however, necessitates the synthesis of an optically active manganese complex catalyst of complicated molecular structure. The other is effected by oxidizing 1-indanone or 2-indanone with a special enzyme. According to this process, treating 1-indanone with naphthalene deoxygenase gives (R)2-hydroxy-1-indanone, but the product shows a low optical purity of 22%. On the other hand, treating 2-indanone with naphthalene deoxygenase gives (S)2-hydroxy-1-indanone, but none of the (R) for m. The latter process requires a special enzyme and is not applicable to the cases where the target is a substance of (R) form with high optical purity [Reskich, S. M. et al. Appl. Environ. Microbiol., 60, 3323 (1994)].
In consequence, there has been a demand for development of a simple process for preparing optically active 2-hydroxy-1-indanones of high optical purity.
The following processes are known for the preparation of cis-1-amino-2-indanol: indene is subjected to addition reaction with iodine isocyanate (INCO) and then treated with methanol, the resulting .beta.-iodocarbamate is heated to give oxazolidone, and the oxazolidone is hydrolyzed (J. Org. Chem., 1967, 32, 540); indene is converted in two steps to trans-1-amino-2-indanol, which is treated successively with benzoyl chloride and thionyl chloride, and the resulting oxazoline is hydrolyzed (J. Am. Chem. Soc., 1951, 73, 1639 and J. Med. Chem., 1992, 35, 1685); 1-methoxycarbonyl-2-indanone is converted in three steps to .beta.-hydroxylcarbamate, which is converted to oxazolidone and hydrolyzed (Tetrahedron, 1991, 47, 4941); indene is converted to indene oxide, indan-1,2-diol, or 2-bromo-1-indanol and then allowed to react with acetonitrile in the presence of sulfuric acid to give oxazoline, which is hydrolyzed (Tetrahedron Lett., 1995, 36, 3993); 2-hydroxy-1-indanone-o-benzyloxime is reduced with borane in tetrahydrofuran (Tetrahedron Lett., 1991, 32, 711).
Any of these processes, however, requires an increased number of reaction steps and expensive reactants to place the amino and hydroxyl groups in cis configuration and faces a number of problems in its application on a commercial scale.
Moreover, in the cases where indan derivatives such as cis-1-amino-2-indanol and its derivatives are used as synthetic intermediates for pharmaceuticals, they at times need to be optically active. If such is the case, it is advantageous to carry out optical resolution in the earliest possible stage in the course of the preparation because the yield of the object indan derivatives is reduced to approximately 1/2 during optical resolution.
Accordingly, it is an object of this invention to provide a process being applicable with ease on a commercial scale for first preparing optically active 2-hydroxy-1-indanone with the use of microbes and then preparing optically active cis-1-amino-2-indanol from said optically active 2-hydroxy-1-indanone, the latter process being applicable with ease on a commercial scale.
Another object of this invention is to provide a process for preparing optically active 2-hydroxy-1-indanone with the use of microbes.
A further object of this invention is to provide a process, readily applicable on a commercial scale, for preparing 2-indanol derivatives, in particular, cis-1-amino-2-indanol.